Italy

Milan, Florence, pISA, ROme, Amalfi Coast & Venice

Yay! You're Planning a Trip to Italy!

So, you’re thinking about visiting Italy—how exciting! Whether you’re still dreaming of this adventure or already have your trip booked, you’re probably wondering where to begin. Which cities should you explore? What are the must-see sights and unforgettable experiences? Don’t worry—I’ve got you covered!

In this post, I’m sharing the detailed itinerary from my two-week journey across Italy. You’ll find a day-by-day breakdown of the cities we visited and the highlights we loved to help you craft your own dream adventure.

Of course, Italy has so many incredible places to see, and while I wish I could have explored more, this itinerary was the perfect fit for us. Hopefully, it sparks some ideas and inspires your own unique trip to this beautiful country. Buon viaggio!

Itinerary Summary:

Our trip started in Milan and we worked our way down Italy!

Milan: 2 days

Florence: 3 days

Rome: 3 days

Amalfi Coast: 2 days

Venice: 2 days

Booked Activities:

Here all the links to the activities I booked during my trip!

Day 1: Milan

Welcome to Italy! Your first full day!

Morning: Visit Duomo di Milano, climb its rooftop for stunning views, and admire the gothic architecture. Go inside the church as well to see the beautiful cathedral.

Afternoon: Shop or browse the iconic Galleria Vittorio Emanuele II and explore Piazza Mercanti. Grab your first gelato in one of the shops!

Evening: Have dinner at Crazy Pizza for a fun pizza show and delicious food. End the night sipping wine at a rooftop bar, soaking in the Milanese sunset.

Day 2: Milan

Tip: For Day 2, I recommend taking a day trip from Milan to Lake Como. This was something we did not do on our trip, and definitely wished we could’ve seen! However, if you want to explore more of Milan and the different neighborhoods, this is where we went!

Morning: Head to Castello Sforzesco, a medieval castle from the 15th century, and roam around the free courtyard and gardens. You can also go inside to explore the museum and exhibitions.

Afternoon: After the castle, we walked over to the neighborhood next door, Brera. An artistic area with lots of shops and art galleries. Grab some lunch at Osteria da Fortunata.

Evening: Head to Navigli to end the day. Navigli is a popular and charming neighborhood in Milan, known for its canals and charming streets, and lively scene with many bars and restaurants! We definitely had lots of drinks enjoying the night!

Day 3: Florence

Time to head to Florence! Only a 2 hour train ride from Florence!

Morning: Head to Florence!

Afternoon: Wander around Florence! Grab some lunch at the most delicious sandwich shop, All’Antico Vinaio. Stroll across Ponte Vecchio, the oldest bridge in Florence, with its unique shops and jewelers. Make sure to find a Wine Window to experience the charm and magic of Florence.

Evening: Lastly, head to the Cathedral of Santa Maria del Fiore, the most important landmark in Florence and one of the most breathtaking sights in all of Italy.

Day 4: Florence

Time for some history and museums!

Morning: Dive into art history at the Accademia Gallery and meet Michelangelo’s David. There were also many beautiful paintings and sculptures to see!

Afternoon: Grab lunch and a drink in the city center. Take a leisurely walk, discovering hidden gems of Florence.

Evening: Wander Piazzale Michelangelo for a breathtaking sunset over the city.

Day 5: Day Trip to Pisa & Cooking Class

This rooftop cooking class was one of the highlight of our trip! Still have not gotten over the view overlooking the heart of Florence while cooking pasta and Tiramisu!

Morning: A quick train to Pisa to visit the iconic Leaning Tower.

Afternoon: Grab some lunch in Pisa and head back to Florence!

Evening: Wrap up your day with a cooking class, perfecting your Italian culinary skills! One of the highlights of our trip, taking a rooftop cooking class, overseeing all of Florence.

Day 6: Rome

Time to head to Rome! Only a 2 hour train ride from Florence!

Morning: Enjoy final breakfast in Florence!

Afternoon: Head to Rome!

Evening: Wander around the heart of Rome and take a magical walk to the Colosseum—a perfect first glimpse of the Eternal City under the stars.

Day 7: Rome

Embrace all the history Rome has to offer!

Morning: Wake up bright and early to go inside the Colosseum and witness the arena! Recommend a tour guide to learn about the history that took place inside the Colosseum about 1,500 years ago!

Afternoon: Explore the grandeur of the Roman Forum and climb Palatine Hill for panoramic views.

Evening: Toss a coin into the Trevi Fountain to ensure your return to Italy.

Day 8: Vatican City

Tip: Make sure to check which days you are in Rome for, since every Wednesday the Pope offers a free service to the people in Saint Peter’s Square. Need to register for tickets in advance, and you will find out if you are selected to attend his service on Tuesday, the day before the service!

Morning: My group was lucky enough to be selected for the Pope’s service so we started the day bright and early at St. Peter’s Square at 6:30 am.

Afternoon: Grab some lunch and visit to the Vatican Museum, where the Sistine Chapel leaves you in awe.

Evening: Go inside Saint Peter’s Church.

Day 9: Amalfi Coast

Time for some beach! Definitely one of the most beautiful cities in Italy and wish we had stayed an extra day longer!

Morning: Time to head to Amalfi Coast! Take the train from Rome to Naples, then for fastest route to Amalfi Coast, take a 1 hour taxi from the Naples Station to Amalfi Coast. Very scenic, but very curvy roads driving through the mountains.

Afternoon: Relax on the beaches, taking in the sun and sea.

Evening: Dine al fresco by the water—pure bliss! Enjoy the cute town and souvenir shopping with yellow and lemons everywhere. Even find some gelato served in a lemon!

Day 10: Boat Tour on Amalfi Coast

This boat tour was definitely one of the highlights of our trip and a must when visiting Amalfi Coast!

Morning: Grab some Breakfast then head to the boat dock.

Afternoon: Enjoy a full day at sea in the Amalfi coast with breathtaking views. The tour we did was 6 hours and included sightseeing the route to Positano and the coast of Ravello, hidden caves, and natural arches. During the tour we got to stop for swimming, snorkeling and cliff jumping. For lunch we got to stop at a restaurant on the sea! Couldn’t have had a better experience!

Evening: Enjoy your final dinner in the beautiful town.